Vaccenyl acetate

11-cis-Vaccenyl acetate (cVA) is a volatile chemical compound that acts as a pheromone in Drosophila and at least one species of longhorn beetle. It is the acetate ester of vaccenyl alcohol.

11-cis-Vaccenyl acetate
Names
Preferred IUPAC name
(11Z)-Octadec-11-en-1-yl acetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C20H38O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-20(2)21/h8-9H,3-7,10-19H2,1-2H3/b9-8- ☒N
    Key: QSZKEDWVAOAFQY-HJWRWDBZSA-N ☒N
  • InChI=1/C20H38O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-20(2)21/h8-9H,3-7,10-19H2,1-2H3/b9-8-
    Key: QSZKEDWVAOAFQY-HJWRWDBZBI
  • CCCCCC/C=C\CCCCCCCCCCOC(=O)C
Properties
C20H38O2
Molar mass 310.51 g/mol
Related compounds
Related compounds
 cis-vaccenic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The odorant receptor subunit Or67d was shown to be necessary for detection of cVA.[1] Males that are mutant for Or67d start courting other males, whereas females that lack Or67d become less receptive towards males courting them.[2] The sensory neurons expressing Or67d send projections to the glomerulus DA1.[3] DA1 is one of the three glomeruli that is bigger in males than in females. Moreover, the projection neurons that connect to DA1 have sexually dimorphic arborizations in the higher brain centers (esp. lateral horn).

References
  1. Ha, TS, Smith DP J. Neurosci. 26:8727-8733 (2006).
  2. A. Kurtovic, A. Widmer, B. J. Dickson, Nature 446, 542 (2007).
  3. Couto A, Alenius M, Dickson BJ.; Curr Biol. 2005 Sep 6;15(17):1535-47.

A Ray, A Zunic, RL Alten, JS McElfresh, LM Hanks, JG Millar. 2011. J. Chem. Ecol. 37:173-178.

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